Honestly, I’m not much of a hat person. I have trouble figuring out what to wear with a hat so it looks like an outfit, not an Indiana Jones costume. But I’m working through it, guys! And as I work through it, I thought I’d share with you a few fun ways I found to get into hat-wearing.

1. Glam. I completely envy those ladies who can just throw on a concert tee and some chap-stick and they’re ready. These are the coveted “low-maintenance” girlfriends. And that works for some people. That does not work for me. I can spend HOURS in front of the mirror on a Friday night, curling my hair and getting my outfit juuuust right. But sometimes the lipstick + hairdo + heels + jewelry + cocktail dress start to look like I’m trying too hard. Enter the floppy-brim fedora. It adds just the right amount of nonchalance and downtown cool to an outfit — much like a sweet throat tattoo, but without the pain and the lifetime commitment.

2. Boho. There’s a reason you’ve seen this pairing a bazillion times: peasant blouses and big floppy-brim hats were just made for each other. Styling a fedora with a bohemian outfit is super simple and chic. It’s an easy was to add a little something extra to a casual look. The trick with this is to make sure you don’t go too boho.

I can’t count the number of times I’ve started out with a fun peasant blouse and a pair of wide-leg jeans. Then I add some groovy platform sandals. Then I swap out the jeans for a tiered maxi skirt. Then I grab a suede fringe bag, throw a damn flower crown on top of my fedora, and add some round sunglasses. Suddenly I look like some weird flower child/Little House on the Prairie extra. Just don’t.

I recommend either going with a peasant blouse and cutoffs/skinnies, or doing a simple tee and wide-leg jeans. Add your awesome hat and you totally just nailed the carefree bohemian look without going overboard. You could also rock this style in winter with boots, skinnies, and one of those big drape-y cardigan things.

3. All black. In a concertgoing, nastygal-chic kind of way. Pair with ankle boots and a black fringe purse for maximum cool-girl aesthetic, or throw on some black skinny jeans and a worn in tee. Maybe get some sleeve tats. Maybe not. That part is up to you.

So what do you guys think? Any tips on how I should wear hats? How do you style your fedoras/ flat brims/ beanies/ fascinators/ derbys/ umm…top hats? Is that a thing? It will be soon. Trust me, it will be soon.

h&m floppy fedora (lots of options here, they even have them in “curve” – for people with curvy heads, I guess??), express tweed dress (similar here and here)

No, it’s not a Rag and Bone fedora. My sister has one of those beauties and every time I see her wearing it I want to snatch it off her pretty blonde head. So when I came across this little baby at H&M, I grabbed it, planted it on my noggin, and walked around the store, taunting the other shoppers with my awesome find (it was the last one!). It only cost me $20, and Andrew Jackson and I happily parted ways at the cash register.

PS: my right arm is looking super-svelte in this picture! I don’t know how that happened. Hello Sarah Connor!